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$57+ Cheap flights from Chicago (CHI) to Ocala, FL

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
Feb 4 — Feb 111
Tue 2/4
Tue 2/11
1 adult, Economy
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The best prices from Chicago to Ocala are usually found in May or April, booked 30 days in advance, depart on a Tuesday or Saturday and return on a Friday

Cheap flight deals from Chicago to Ocala

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Ocala (OC4). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$125
(Cheapflightsfares)

One-way from

$57
(Cheapflightsfares)

Popular in

December

Cheapest in

May

Average price

$265
Provider with most accurate pricing for Chicago (CHI)-Orlando (ORL) flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Orlando (ORL) flights.
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From Chicago (CHI) to Ocala
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One-way flight from Chicago (CHI) to Ocala
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Highest demand for flights based on searches. 10% potential increase in price ($32 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in January 2025
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Find flight deals from Chicago to Ocala

Cheapest flights from Chicago to Ocala
Explore the most affordable flight options available from Chicago to Ocala. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 30, 2025.

This CheapOair deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/287:18 pmORD - MCO
Nonstop2h 58mMultiple Airlines
Fri 3/76:44 pmMCO - ORD
1 stop6h 12mMultiple Airlines
Deal found 1/29$125
This Cheapflightsfares deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1212:58 pmMDW - MCO
Nonstop2h 53mFrontier
Sun 4/137:25 amMCO - MDW
Nonstop2h 59mFrontier
Deal found 1/29$125
This Booking.com deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/15:45 pmORD - MCO
Nonstop2h 46mSpirit Airlines
Thu 3/69:16 pmMCO - ORD
Nonstop3h 12mSpirit Airlines
Deal found 1/29$126
This Frontier deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/210:59 amORD - MCO
Nonstop2h 52mFrontier
Fri 2/76:37 pmMCO - ORD
Nonstop3h 20mFrontier
Deal found 1/29$134
This Southwest deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/37:05 pmMDW - MCO
Nonstop2h 40mSouthwest
Wed 3/129:05 pmMCO - MDW
Nonstop2h 55mSouthwest
Deal found 1/28$184
This Delta deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/252:08 pmMDW - MCO
1 stop6h 05mDelta
Thu 2/276:15 amMCO - MDW
1 stop4h 57mDelta
Deal found 1/29$204
This Southwest deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/257:00 amORD - MCO
2 stops8h 25mSouthwest
Wed 2/263:25 pmMCO - ORD
1 stop7h 55mSouthwest
Deal found 1/30$216

Find flights from Chicago to Ocala within your budget

Customize your flight search to find flights from Chicago to Ocala that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 30, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Fri 2/28

7:18 pm-11:16 pm

Nonstop2h 58m

Orlando

Fri 3/7

7:30 am-9:44 am

Nonstop3h 14m

$125

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 4/12

12:58 pm-4:51 pm

Nonstop2h 53m

Orlando

Sun 4/13

7:25 am-9:24 am

Nonstop2h 59m

$125

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sat 3/1

5:45 pm-9:31 pm

Nonstop2h 46m

Orlando

Sat 3/8

7:30 am-9:44 am

Nonstop3h 14m

$126

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Thu 4/3

5:00 pm-12:18 am

1 stop6h 18m

Orlando

Fri 4/11

8:00 am-12:42 am

1 stop17h 42m

$127

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 3/3

7:05 pm-10:45 pm

Nonstop2h 40m

Orlando

Wed 3/12

9:05 pm-11:00 pm

Nonstop2h 55m

$184

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 2/25

2:08 pm-9:13 pm

1 stop6h 05m

Orlando

Thu 2/27

6:15 am-10:12 am

1 stop4h 57m

$204

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Tue 2/25

7:00 am-4:25 pm

2 stops8h 25m

Orlando

Fri 2/28

6:20 am-2:00 pm

1 stop8h 40m

$216

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Wed 3/12

11:44 am-7:34 pm

1 stop6h 50m

Orlando

Sat 3/22

6:00 am-12:00 pm

1 stop7h 00m

$261

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Thu 2/27

4:21 pm-12:42 am

1 stop7h 21m

$57

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sun 2/16

12:48 pm-11:29 pm

1 stop9h 41m

$58

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

Showing 1-10 of 23 results
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Best time to book a flight from Chicago to Ocala

Have a flexible travel schedule? Discover the best time to fly to Ocala from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Chicago to Ocala

Get recent, data-driven insights about flights from Chicago to Ocala including ideal travel times, pricing trends, and more.

How far ahead should I book a flight from Chicago to Ocala?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Ocala. Price data was last updated on January 24, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Ocala, you should look to book at least 30 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago to Ocala?

Currently, May is the cheapest month in which you can book a flight from Chicago to Ocala (average of $206). Flying from Chicago to Ocala in November is currently the most expensive (average of $289). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to OC4?

Find hourly flight availability from Chicago to Ocala. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 30, 2025.

When flying from Chicago to Ocala, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Chicago to Ocala?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Ocala. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Ocala flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Ocala

Explore weekly flight availability from Chicago to Ocala. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated January 30, 2025.

The most flights from CHI to OC4 are scheduled on a Thursday (60 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (45 on average).

Rainfall in Ocala by month

Plan your trip to Ocala by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Ocala ranges from 2.4 - 8.7 inches per month. June is typically the wettest month, when rainfall can reach 8.7 in. November is typically the driest time to visit Ocala when rainfall is around 2.4 in.

Temperature in Ocala by month

Plan your trip to Ocala by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Ocala, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 60.8 F).

Reviews of airlines servicing Ocala

Get insights into the airlines that provide service to Ocala. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Ocala. Reviews last updated January 30, 2025.
To help decide which airline to fly from Chicago to Ocala, see what other customers have to say about Southwest, Delta and JetBlue. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Southwest
8.1
Very good
4,585 reviews
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Delta
8.0
Very good
8,450 reviews
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

JetBlue
7.4
Good
3,153 reviews
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

United Airlines
7.4
Good
8,906 reviews
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Ocala. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Chicago to Ocala one-way?

    One-way options have recently been found by users for as low as $57 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $58 and JetBlue from $99 one-way.

  • What are the most reliable airlines from Chicago to Ocala?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago to Ocala on time: Azul (89%), Southwest (89%), Brussels Airlines (84%).

  • What are the cheapest flights from Chicago to Ocala?

    While on average a flight from Chicago to Ocala is generally $555, our data shows the cheapest flight currently is $53. When looking at the most popular route, (Chicago O'Hare Intl - Orlando), you can expect to pay $50 for that flight.

  • Can I find deals for flights from Chicago to Ocala that include hotel bookings?

    Yes. In addition to deals on Chicago to Ocala flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Ocala?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Ocala.

  • Can I find deals for business class flights from Chicago to Ocala?

    Yes. Cheapflights offers flight deals from Chicago to Ocala by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Ocala?

    Currently, May is the cheapest month in which you can book a flight from Chicago to Ocala (average of $206). Flying from Chicago to Ocala in November is currently the most expensive (average of $289). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Top 7 airlines flying from Chicago to Ocala

Discover the top 7 airlines that operate flights from Chicago to Ocala. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$44Average$192FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$58Average$169FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$106Average$213FlexibilityNo cancel feeOn-time88%
American AirlinesCheapest$157Average$417FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$159Average$363FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$172Average$399FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$438FlexibilityNo cancel feeOn-timeN/A
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